*deep breath* It could work. I can really see it working and I think it's hilarious that Alex Hirsch ships them.

Stitch would love the attention from Dipper and Dipper would appreciate Stitch actually listening and taking into consideration all of his "crazy" theories.

Plus the pure PANIC that Dipper could instill with Stitch with all the shenanigans he goes through is untapped comedy gold. (remember that scene in lilo and stitch 2 when lilo deliberately jumped “to her death”?)